5297-45-0

Upstream product

• 104-53-0 3-phenyl-propionaldehyde 
• 55962-05-5 [N-(p-tolylsulfonyl)imino]phenyliodinane 
• 21849-40-1 dibromamine-T 
• 67333-73-7 1-nitro-4-phenylbutan-2-one 
• 92755-81-2 N-bromo-p-toluenesulfonamide 
• 70-55-3 toluene-4-sulfonamide 
• 645-45-4 hydrocinnamic acid chloride 
• 41085-71-6 bromamine T 
• 141377-53-9 1-nitro-4-phenylbutan-2-ol 

Relevant academic research and scientific papers

Formation of esters and amides via metal-free Csp2-Csp3 bond cleavage of α-nitro ketone: Mechanistic insight to the reaction pathway

A catalyst free protocol for hucleophilic Csp2-Csp3 bond cleavage of a-nitroketone has been achieved for the formation of C-O and C-N bond. A series of differently substituted a-nitroketones could be selectively cleaved and converted into corresponding esters and tosylamides in presence of alcohols and bromamine-T respectively. Mechanism of the C-C bond cleavage has been proposed by identifying different reaction intermediates using IR and NMR spectroscopic methods.

Unexpected C-C bond cleavage of α-nitroketone in the presence of TsNBr2: A new pathway for C-N bond formation

A new catalyst-free protocol for C-N bond formation via the cleavage of α-nitroketone has been developed. When α-nitroketones are treated with TsNBr2 in the presence of potassium carbonate, unexpected cleavage of C(O)-CHNO2 bond of α-nitroketone was observed followed by the formation of corresponding amide. Various nitroketones could be converted to corresponding amide using this procedure.

Formation of new C-O and C-N bonds via base promoted Csp2-Csp3 bond cleavage of α-nitro ketone

A catalyst free protocol has been developed for nucleophilic Csp2-Csp3 bond cleavage of α-nitroketone in the presence of potassium carbonate to create new C-O and C-N bonds. A series of different substituted α-nitroketones could be selectively cleaved and converted into corresponding esters and tosylamides in the presence of alcohols and bromamine-T, respectively.

Iodide as an activating agent for acid chlorides in acylation reactions

Acid chlorides can be activated using a simple iodide source to undergo nucleophilic attack from a variety of relatively weak nucleophiles. These include Friedel-Crafts acylation of N-methylpyrroles, N-acylation of sulfonamides, and acylation reactions of hindered phenol derivatives. The reaction is believed to proceed through a transient acid iodide intermediate.

A highly efficient catalyst-free protocol for C-H bond activation: Sulfamidation of alkyl aromatics and aldehydes

A catalyst-free protocol has been developed for amidation of alkyl aromatics and aldehydes using TsNBr2via a nitrene transfer process in the presence of a base in excellent yield within a short time. The reaction was found to be selective for secondary and tertiary benzylic C-H bonds and C-H bonds of aldehydic groups.

Iron-catalyzed nitrene insertion reaction for facile construction of amide compounds

A facile method for the construction of amide compounds from aldehydes by an iron-catalyzed nitrene insertion reaction has been developed. Both aryl and aliphatic aldehydes can directly afford the corresponding amides with an iron(II)-terpyridine (tpy) complex formed in situ as catalyst, and PhI=NTs as nitrogen source under mild reaction conditions. An ESI-MS study revealed the formation of [Fe(tpy)NTs)]+ as a reaction intermediate. Georg Thieme Verlag Stuttgart - New York.

Iron(II)-catalyzed amidation of aldehydes with iminoiodinanes at room temperature and under microwave-assisted conditions

A method for the amidation of aldehydes with PhI=NTs/PhI=NNs as the nitrogen source and an inexpensive iron(II) chloride + pyridine as the in situ formed precatalyst under mild conditions at room temperature or microwave assisted conditions is described. The reaction was operationally straightforward and accomplished in moderate to excellent product yields (20-99%) and with complete chemoselectivity with the new C-N bond forming only at the formylic C-H bond in substrates containing other reactive functional groups. By utilizing microwave irradiation, comparable product yields and short reaction times of 1 h could be accomplished. The mechanism is suggested to involve insertion of a putative iron-nitrene/imido group to the formylic C-H bond of the substrate via a H-atom abstraction/radical rebound pathway mediated by the precatalyst [Fe(py)4Cl2] generated in situ from reaction of FeCl 2 with pyridine.

Highly efficient ruthenium(II) porphyrin catalyzed amidation of aldehydes

H to N: The first example of a mild, highly efficient C-H bond amidation catalyzed by ruthenium(II) porphyrin complexes uses PhI=NTs as the nitrogen source for installing the amide bond functionality in a wide variety of aldehydes (see scheme). The protocol is chemoselective, with the new C-N bond forming only at the acyl C-H bond, even in aldehyde substrates containing other functional groups.